Department of Chemistry, Indian Institute of Technology Kharagpur, Kharagpur-721302, India.
Photochem Photobiol Sci. 2012 Oct;11(10):1558-66. doi: 10.1039/c2pp25091h.
1-(Hydroxyacetyl)pyrene has been introduced as a new fluorescent phototrigger for alcohols and phenols. Alcohols and phenols were protected as their corresponding carbonate esters by coupling with fluorescent phototrigger, 1-(hydroxyacetyl)pyrene. Photophysical studies of caged carbonates showed that they all exhibited strong fluorescence properties. Irradiation of the caged carbonates by visible light (≥410 nm) in aqueous acetonitrile released the corresponding alcohols or phenols in high chemical (95-97%) and quantum (0.17-0.21) yields. The mechanism for the photorelease was proposed based on Stern-Volmer quenching experiments and solvent effect studies. Importantly, 1-(hydroxyacetyl)pyrene showed as a phototrigger for rapid photorelease of the biologically active molecule adenosine. In vitro biological studies revealed that 1-(hydroxyacetyl)pyrene has good biocompatibility, cellular uptake property and cell imaging ability.
1-(羟基乙酰基)苝已被引入作为醇和酚的新型荧光光解试剂。醇和酚通过与荧光光解试剂 1-(羟基乙酰基)苝的偶联反应，被保护为相应的碳酸酯。对笼状碳酸酯的光物理研究表明，它们都表现出很强的荧光性质。在水-乙腈中用可见光（≥410nm）辐照笼状碳酸酯，可以以高化学收率（95-97%）和量子收率（0.17-0.21）释放相应的醇或酚。基于 Stern-Volmer 猝灭实验和溶剂效应研究，提出了光解释放的机理。重要的是，1-(羟基乙酰基)苝可以作为快速光解生物活性分子腺苷的光解试剂。体外生物学研究表明，1-(羟基乙酰基)苝具有良好的生物相容性、细胞摄取特性和细胞成像能力。
